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Cheap flights from Chicago Midway Airport to Milan from $289

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 8/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$782Delta
Mon, Aug 3 - Wed, Aug 19
KLM Logo
1:05 pm - 10:55 am
MDW
-
MXP
14h 50m
1 stop
KLM Logo
1:05 pm - 10:10 pm
MXP
-
MDW
16h 05m
1 stop
$784KLM
Mon, Dec 7 - Tue, Dec 22
Delta Logo
12:41 pm - 9:25 am
MDW
-
MXP
13h 44m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$791Delta
Wed, Jul 29 - Thu, Aug 20
Delta Logo
12:46 pm - 10:25 am
MDW
-
MXP
14h 39m
2 stops
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$795Delta
Wed, Aug 19 - Wed, Aug 26
Delta Logo
12:46 pm - 12:05 pm
MDW
-
MXP
16h 19m
2 stops
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$796Delta
Mon, Aug 3 - Wed, Aug 19
KLM Logo
4:39 pm - 9:25 am
MDW
-
MXP
33h 46m
1 stop
KLM Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$797KLM
Sat, Aug 8 - Fri, Aug 21
Delta Logo
1:25 pm - 10:25 am
MDW
-
MXP
14h 00m
2 stops
Delta Logo
9:00 am - 10:36 pm
MXP
-
MDW
20h 36m
2 stops
$800Delta
Wed, Aug 19 - Wed, Aug 26
Air France Logo
1:51 pm - 11:20 am
MDW
-
LIN
14h 29m
2 stops
Air France Logo
12:20 pm - 10:36 pm
LIN
-
MDW
17h 16m
2 stops
$844Air France
Mon, Aug 3 - Wed, Aug 19
Air France Logo
1:51 pm - 11:20 am
MDW
-
LIN
14h 29m
2 stops
Air France Logo
12:20 pm - 10:36 pm
LIN
-
MDW
17h 16m
2 stops
$846Air France
Mon, Aug 3 - Wed, Aug 19
Multiple Airlines Logo
1:25 pm - 10:05 am
MDW
-
LIN
13h 40m
2 stops
Multiple Airlines Logo
12:20 pm - 10:36 pm
LIN
-
MDW
17h 16m
2 stops
$959Multiple Airlines
Tue, Aug 18 - Tue, Aug 25

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KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets
KLM
Dec 7
MDW1:05 pmChicago Midway
14h 50m
1 stop
MXP10:55 amMilan Malpensa
Dec 22
MXP1:05 pmMilan Malpensa
16h 05m
1 stop
MDW10:10 pmChicago Midway
$784
KLM
Aug 8
MDW4:39 pmChicago Midway
33h 46m
1 stop
MXP9:25 amMilan Malpensa
Aug 21
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$797
KLM
Aug 21
MDW12:46 pmChicago Midway
13h 39m
1 stop
MXP9:25 amMilan Malpensa
Aug 28
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$834

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets
Delta
Aug 3
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$782
Delta
Jul 29
MDW12:41 pmChicago Midway
13h 44m
1 stop
MXP9:25 amMilan Malpensa
Aug 20
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$791
Delta
Aug 19
MDW12:46 pmChicago Midway
14h 39m
2 stops
MXP10:25 amMilan Malpensa
Aug 26
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$795

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Milan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 9, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$782
Quickest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 12/7

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Tue 12/22

1:05 pm-10:10 pm

1 stop16h 05m

$784

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 7/29

12:41 pm-9:25 am

1 stop13h 44m

Milan Malpensa

Thu 8/20

11:40 am-10:36 pm

1 stop17h 56m

$791

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/19

12:46 pm-10:25 am

2 stops14h 39m

Milan Malpensa

Wed 8/26

11:40 am-10:36 pm

1 stop17h 56m

$795

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

12:46 pm-12:05 pm

2 stops16h 19m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$796

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 8/8

4:39 pm-9:25 am

1 stop33h 46m

Milan Malpensa

Fri 8/21

11:40 am-10:36 pm

1 stop17h 56m

$797

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/19

1:25 pm-10:25 am

2 stops14h 00m

Milan Malpensa

Wed 8/26

9:00 am-10:36 pm

2 stops20h 36m

$800

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 8/3

1:51 pm-11:20 am

2 stops14h 29m

Milan Linate

Wed 8/19

12:20 pm-10:36 pm

2 stops17h 16m

$844

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 8/3

1:51 pm-11:20 am

2 stops14h 29m

Milan Linate

Wed 8/19

12:20 pm-10:36 pm

2 stops17h 16m

$846

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Tue 8/18

1:25 pm-10:05 am

2 stops13h 40m

Milan Linate

Tue 8/25

12:20 pm-10:36 pm

2 stops17h 16m

$959

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Friday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,337. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,526.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

12h 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan takes 12h 25m
There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Milan

  • How far is Chicago Midway to Milan by plane?

    Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 25m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milan?

    Prices for flights from Chicago Midway Airport to Milan are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milan?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

  • What documentation or ID do you need to fly to Milan?

    The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Stresa
Brescia
Livigno
Lecco
Monza
Domodossola
Menaggio
Bellano
Assago
Crema
Cernobbio
Levanto
Moltrasio
Baveno
Bormio
Rho
Iseo
Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport